Timex Easy Reader

Here, we start off pretty humble: the Timex Easy Reader. For around $25 (or the bargain bin at Walmart) you can get a perfectly suitable watch without flash or substance, but with a perfectly classic look that can go in pretty much any informal setting.

As for the internals, you get what you pay for. This is basically the Toyota Corolla of watches. It'll blend in, but don't expect it to go from 0-60 in five seconds.

Rolex Submariner

The Rolex Submariner has been at the forefront of the minds of the watch-illiterate public for much of its existence. No matter what one might know about watches, ask them to point out a Submariner and most men, women, and children could reliably do it.

Why? Because the diver is the platonic ideal of the classic watch. It's got the unique characteristics and heritage to back it up. Oh, and it's also bulletproof.

If the Timex is a Toyota, the Rolex is the Rolls-Royce.

That heritage comes at a price: The most basic model starts at about $7,500.